- The Ritter reaction under incredibly green protocol: Nano magnetically silica-supported Br?nsted acid catalyst
-
HClO4-functionalized silica-coated magnetic nanoparticles [γ-Fe2O3@SiO2-HClO4] (2.5 mol%) has been found to be a capable biocompatible and recyclable catalyst for highly efficient conversion of a variety of alcohols to corresponding amides via modified Ritter reaction in good to excellent yields. Since this heterogeneous catalyst can be simply removed by using an external magnetic device then recovered, it also enhances product purity and promises economic.
- Ma'mani, Leila,Heydari, Akbar,Sheykhan, Mehdi
-
-
Read Online
- o-Benzenedisulfonimide as a reusable Bronsted acid catalyst for Ritter-type reactions
-
Reactions between various benzyl alcohols or tert-butyl alcohol and nitriles were carried out in the presence of catalytic amounts (usually 10-20 mol-%) of o-benzenedisulfonimide as a Bronsted acid catalyst; the reaction conditions were mild and the yields of amides were good. The catalyst was easily recovered and purified, ready to be used in further reactions, with economic and ecological advantages. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Barbero, Margherita,Bazzi, Stefano,Cadamuro, Silvano,Dughera, Stefano
-
-
Read Online
- Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides
-
An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.
- Yaragorla, Srinivasarao,Singh, Garima,Lal Saini, Pyare,Reddy, M. Kesava
-
-
Read Online
- Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
-
Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
- Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
-
-
Read Online
- Reaction Route and Mechanism of the Direct N-Alkylation of Sulfonamides on Acidic Mesoporous Zeolite β-Catalyst
-
Development of highly active heterogeneous catalysts with strong acidity and mesoporous structure is a highly attractive strategy for organic synthesis. In this study, a mesoporous zeolite beta (HBeta-M) with bulky particle size and strong acidity was synthesized and used in the direct N-alkylation of sulfonamides with alcohols. The strongly acidic HBeta-M had a higher intrinsic activity with initial turnover frequency of 11 × 10-2 s-1 than those of H-form mordenite nanosheets (3.3 × 10-2 s-1) and montmorillonite (4.0 × 10-2 s-1) catalysts. The experiment and characterization results demonstrate that there are two parallel reaction routes on the acidic catalysts. One route is the reaction of benzhydrol with p-toluenesulfonamide (route I). Another route is the reaction of dibenzhydryl ether, arising from route I, with p-toluenesulfonamide (route II), which is found in this work. The reaction rate of route I (13 × 10-3 mol kg-1 s-1) was higher than that of route II (9.8 × 10-3 mol kg-1 s-1) on HBeta-M, but route II predominantly contributed to the formation of the target product with high selectivity. Hereby, a complete reaction mechanism is proposed in this work.
- Fu, Wenqian,Shen, Runsheng,Bai, Enhui,Zhang, Lei,Chen, Qun,Fang, Zhongxue,Li, Guangchao,Yi, Xianfeng,Zheng, Anmin,Tang, Tiandi
-
p. 9043 - 9055
(2018/09/11)
-
- Chemoproteomics-enabled covalent ligand screen reveals a cysteine hotspot in reticulon 4 that impairs ER morphology and cancer pathogenicity
-
Chemical genetics has arisen as a powerful approach for identifying novel anti-cancer agents. However, a major bottleneck of this approach is identifying the targets of lead compounds that arise from screens. Here, we coupled the synthesis and screening of fragment-based cysteine-reactive covalent ligands with activity-based protein profiling (ABPP) chemoproteomic approaches to identify compounds that impair colorectal cancer pathogenicity and map the druggable hotspots targeted by these hits. Through this coupled approach, we discovered a cysteine-reactive acrylamide DKM 3-30 that significantly impaired colorectal cancer cell pathogenicity through targeting C1101 on reticulon 4 (RTN4). While little is known about the role of RTN4 in colorectal cancer, this protein has been established as a critical mediator of endoplasmic reticulum tubular network formation. We show here that covalent modification of C1101 on RTN4 by DKM 3-30 or genetic knockdown of RTN4 impairs endoplasmic reticulum and nuclear envelope morphology as well as colorectal cancer pathogenicity. We thus put forth RTN4 as a potential novel colorectal cancer therapeutic target and reveal a unique druggable hotspot within RTN4 that can be targeted by covalent ligands to impair colorectal cancer pathogenicity. Our results underscore the utility of coupling the screening of fragment-based covalent ligands with isoTOP-ABPP platforms for mining the proteome for novel druggable nodes that can be targeted for cancer therapy.
- Bateman,Nguyen,Roberts,Miyamoto,Ku,Huffman,Petri,Heslin,Contreras,Skibola,Olzmann,Nomura
-
supporting information
p. 7234 - 7237
(2017/07/11)
-
- Manganese(III) acetate catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles
-
Mn-Catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles is disclosed, which enables the synthesis of a broad range of secondary amides in moderate to excellent yields under mild conditions. The interaction between Mn(iii) and DDQ facilitates the oxidation and makes it highly efficient and selective.
- Zhang, Yaxing,Dong, Jianyu,Liu, Lixin,Liu, Long,Zhou, Yongbo,Yin, Shuang-Feng
-
supporting information
p. 2897 - 2901
(2017/04/11)
-
- Method for preparing amide from aryl methane derivative and nitrile
-
The invention provides a simple and efficient method for directly preparing an amide compound from an aryl methane derivative and nitrile. In the method, manganese triacetate dihydrate is used as a catalyst, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) is used as an oxidizing agent. The method has the characteristics that raw materials are cheap and easy to obtain, the source of the nitrile is wide, reaction conditions are mild, the applicability is wide and the like. The method solves the problems that ceric ammonium nitrate (CAN) and a fluorine agent which are used by a method for directly synthesizing amide by using aryl methane and nitrile compounds are hard to treat, atomic economy is poor, the source of the nitrile is narrow and the like.
- -
-
Paragraph 0068-0070
(2017/05/10)
-
- Ritter reactions in flow
-
Flow me a Ritter: Ritter reactions are performed in a simple microreactor setup using tert-butylacetate as versatile carbocation source. The protocol avoids the handling of large amounts of hot concentrated sulfuric acid as low concentrations are optimal for rapid access tert-butyl- or diphenylmethyl- protected amides. Copyright
- Audiger, Logan,Watts, Kevin,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
-
experimental part
p. 257 - 260
(2012/05/04)
-
- Organocatalytic synthesis of amides from nitriles via the Ritter reaction
-
A simple, inexpensive, environmentally friendly, and efficient route for the synthesis of a wide variety of amides in high yields via the Ritter reaction of alcohols with nitriles has been demonstrated. Pentafluorophenyl ammonium triflate (PFPAT) is used as an organocatalyst and is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.
- Khaksar, Samad,Fattahi, Eskandar,Fattahi, Esmail
-
experimental part
p. 5943 - 5946
(2011/11/28)
-
- HClO4-SiO2 as an efficient and recyclable catalyst for the synthesis of amide derivatives
-
An efficient and clean procedure for amide alkylation is reported by direct condensation of equimolar amounts of benzylic and allylic alcohols with primary amides in the presence of silica perchloric acid (HClO4-SiO 2). The direct co
- Song, Weibin,Ma, Lei,Hu, Lihong
-
experimental part
p. 3186 - 3196
(2011/09/20)
-
- Amberlyst-15 in ionic liquid: An efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes
-
The nucleophilic substitution reaction of secondary alcohols and hydroamination of alkenes with amides, sulfonamides, carbamates, and amines using Amberlyst-15 immobilized in [Bmim][BF4] (1-butyl-3- methylimidazolium tetrafluoroborate) ionic liquid as an efficient recyclable reagent is described. The solvent effect is prominent in the reaction, and the desired substitution products are obtained in good to excellent yield. The protocol is advantageous due to the ease of handling of the reagents, the simple work-up procedure, and the environmentally benign conditions that allow effective recyclability. A facile protocol involving Amberlyst-15 in the ionic liquid [Bmim][BF4] (= 1-butyl-3-methylimidazolium tetrafluoroborate) has been developed for nucleophilic substitution of alcohols and hydroamination of alkenes.
- Qureshi, Ziyauddin S.,Deshmukh, Krishna M.,Tambade, Pawan J.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
-
experimental part
p. 6233 - 6238
(2010/12/25)
-
- FeCl3-catalyzed Ritter reaction. Synthesis of amides
-
A safe and inexpensive synthesis of amides, from benzylic alcohols and nitriles and from t-butyl acetate and nitriles, using a Ritter reaction catalyzed by FeCl3·6H2O is described.
- Anxionnat, Bruno,Guérinot, Amandine,Reymond, Sébastien,Cossy, Janine
-
experimental part
p. 3470 - 3473
(2009/09/28)
-
- Polyvinylpolypyrrolidone-supported boron trifluoride: A high-loaded, polymer-supported Lewis acid for the Ritter reaction
-
A Mild and efficient method for preparing amides by reaction of nitriles with benzhydrol and tertiary alcohols is described using polyvinylpolypyrrolidone-supported boron trifluoride. Selective amidation of benzhydrol in the presence of primary benzyl alcohols was also achieved.
- Lakouraj, Moslem Mansour,Mokhtary, Masoud
-
experimental part
p. 53 - 56
(2010/03/30)
-
- Molecular iodine-catalysed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or sulfonamides
-
A highly efficient method for the C-N bond formation via 2 mol% of molecular iodine-catalysed amidation reaction of benzylic and allylic alcohols with carboxamides or sulfonamides in MeCN is described, giving the corresponding substituted amides and allyl
- Lin, Xufeng,Wang, Jun,Xu, Fangxi,Wang, Yanguang
-
experimental part
p. 638 - 641
(2011/03/18)
-
- An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfonamide
-
A simple, inexpensive, environmentally friendly and high yielding amidation reaction of benzylic and allylic alcohols with primary amides using a catalytic amount of FeCl3 (5 mol %) is described. Direct substitution of various amides such as be
- Jana, Umasish,Maiti, Sukhendu,Biswas, Srijit
-
p. 858 - 862
(2008/04/13)
-
- Synthesis of n-benzhydrylamides from nitriles by ritter reactions in formic acid
-
Benzhydrol reacts with nitriles in refluxing formic acid to produce amides arising from the Ritter reaction. This reaction does not require a strong acid catalyst, and the products are isolated without the need for chromatography. The conditions permit the preparation of acrylamides and methacrylamides without polymerization of the nitrile.
- Gullickson, Glen C.,Lewis, David E.
-
p. 681 - 684
(2007/10/03)
-